(2-Methoxyethyl)(methyl)amine → [4-(2-Bromophenyl)-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-3-yl]-N-(2-methoxyethyl)-N-methylamine

HRID 6930

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH3:6].Br[C:8]1[N:9]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Br:31])[C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:17][CH:18]=2)=[N:11][N:12]=1>C(Cl)(Cl)Cl>[Br:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[N:9]1[C:10]([C:13]2[CH:18]=[N:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)=[N:11][N:12]=[C:8]1[N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH3:6]

Participants

Conditions

Temperature: 200 °C

Procedure

In a sealed tube, N-(2-methoxyethyl)methylamine (3 ml) was added to 5-[5-bromo-4-(2-bromophenyl)-4H-1,2,4-triazol-3-yl]-2-phenylpyridine (1.0 g) prepared in the Production Example 3, and stirred at 180° C. for 13 hours and at 200° C. for 24 hours. After the reaction solution was cooled to ambient temperature, chloroform was added to the solution, which was then washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the resulting residue was washed with ethyl acetate, to afford the entitled compound as white solid (711 mg, 70%). The physico-chemical values are as follows.

Workup

customprepared in the Production Example 3
temperatureAfter the reaction solution was cooled to ambient temperature
washwas then washed with saturated aqueous sodium hydrogen carbonate solution
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customAfter the solvent was evaporated under reduced pressure
washthe resulting residue was washed with ethyl acetate

Sources & evidence

ORD record: ord-1e15683ab87d482184ed6c6ba6dd6304
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084164B2

Linked notes

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